Bulletin of the Chemical Society of Japan

Metal (II) d-tartrates catalyzed asymmetric ring opening of oxiranes with various nucleophiles

H Yamashita

Index: Yamashita, Hiroyuki Bulletin of the Chemical Society of Japan, 1988 , vol. 61, p. 1213 - 1220

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Citation Number: 104

Abstract

The asymmetric ring opening of meso-2, 3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal (II) d-tartrates as heterogeneous chiral Lewis acid catalysts. The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal (II) d-tartrate, and Zn (II) d-tartrate gave the best enantioselectivity in the respective reactions of 1, 2-epoxycyclohexane with 1-butanethiol, aniline, and ...